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277762

Sigma-Aldrich

(+)-Methyl D-lactate

greener alternative

98%, optical purity ee: 96% (GLC)

Synonyme(s) :

D-Lactic acid methyl ester, Methyl (R)-(+)-lactate

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About This Item

Formule linéaire :
CH3CH(OH)CO2CH3
Numéro CAS:
17392-83-5
Poids moléculaire :
104.10
Numéro CE :
241-420-6
Numéro MDL:
MFCD00004517
Code UNSPSC :
12352108
ID de substance PubChem :
24856785
Nomenclature NACRES :
NA.22

Pureté

98%

Forme

liquid

Activité optique

[α]21/D +8.4°, neat

Pureté optique

ee: 96% (GLC)

Caractéristiques du produit alternatif plus écologique

Safer Solvents and Auxiliaries
Learn more about the Principles of Green Chemistry.

sustainability

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Indice de réfraction

n20/D 1.413 (lit.)

Point d'ébullition

144-145 °C (lit.)

Densité

1.09 g/mL at 25 °C (lit.)

Autre catégorie plus écologique

, Aligned

Chaîne SMILES 

COC(=O)[C@@H](C)O

InChI

1S/C4H8O3/c1-3(5)4(6)7-2/h3,5H,1-2H3/t3-/m1/s1

Clé InChI

LPEKGGXMPWTOCB-GSVOUGTGSA-N

Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry.This compound has benign qualities and is biodegradable, water miscible, and functions as a versatile solvent for CA membrane preparation. This is also used as an intermediate for the production of other chemicals, polymers, and derivatives. Thus this product has been enhanced for Safer solvents and auxiliaries. Click here for more information.

Application

(+)-Methyl D-lactate can be used as a starting material in the asymmetric preparation of:
  • Neomethymycin, a macrolide which contains 12-membered macrolactone that is used as a potent biological agent.
  • PM-toxin A.

It can also be used as a chiral pool along with D-(-)-tartaric acid in the stereoselective total synthesis of separacenes A and B via Trost-Rychnovsky alkyne rearrangement, Horner-Wadsworth-Emmons olefination as well as Corey-Bakshi-Shibata reaction.

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Warning

Mentions de danger

H226,H319,H335

Classification des risques

Eye Irrit. 2 - Flam. Liq. 3 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

120.2 °F - closed cup

Point d'éclair (°C)

49 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Asymmetric total synthesis of PM-toxin A, a corn host-specificpathotoxin
Hayakawa H, et al.
Chemical Communications (Cambridge, England), 66(13), 1219-1220 (1997)
Total synthesis of neomethymycin and novamethymycin
O Hong-Se and K Han-Young
Tetrahedron, 66(24), 4307-4317 (2010)
A Knüttel et al.
Magnetic resonance in medicine, 9(2), 254-260 (1989-02-01)
An RF and field gradient pulse sequence is presented permitting the single-scan volume-selective spectral editing of the signals of coupled spins. The attribute "single scan" means that the editing of resonance lines is performed in each accumulation or phase cycling
Changhua Xu et al.
Langmuir : the ACS journal of surfaces and colloids, 24(16), 9118-9124 (2008-07-12)
This study reports the development of novel chiral sensors based on the self-assembly of perfunctionalized beta-cyclodextrins (beta-CD) on a quartz crystal microbalance transducer for real time chiral recognition. Ten chiral sensors immobilized with mercaptyl perfunctionalized beta-cyclodextrins were found to exhibit
Philipp Zielke et al.
Physical chemistry chemical physics : PCCP, 8(24), 2826-2830 (2006-06-16)
Raman active symmetric O-H stretching modes are detected and assigned for the first time in isolated methanol, ethanol and methyl lactate trimers, providing insights into cluster structure, vibrational assignments and hydrogen-bond mediated couplings.
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